Synthesis of chiral α-amino aldehydes linked by their amine function to solid support

被引：8
|
作者：
Cantel, S
Heitz, A
Martinez, J
Fehrentz, JA
机构：
[1] Univ Montpellier I, CNRS, UMR 5810, LAPP,Fac Pharm, F-34093 Montpellier 5, France
[2] Univ Montpellier 2, CNRS, UMR 5810, LAPP,Fac Pharm, F-34093 Montpellier 5, France
[3] INSERM, UMR 5048,CNRS, Ctr Biochim Struct, UM1,UMR 554,Fac Pharm, F-34093 Montpellier 5, France
来源：
JOURNAL OF PEPTIDE SCIENCE | 2004年 / 10卷 / 09期
关键词：
alpha-amino aldehyde; Weinreb amide; alpha-amino ketone; solid phase synthesis; reductive amination;
D O I：
10.1002/psc.605
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
The anchoring of an a-amino-acid derivative by its amine function on to a solid support allows some chemical reactions starting from the carboxylic acid function. This paper describes the preparation of aamino aldehydes linked to the support by their amine function. This was performed by reduction with LiAIH(4) of the corresponding Weinreb amide linked to the resin. The aldehydes obtained were then involved in Wittig or reductive amination reactions. In addition, the linked Weinreb amide was reacted with methylmagnesium bromide to yield the corresponding ketone. After cleavage from the support, the compounds were obtained in good to excellent yields and characterized. Copyright (C) 2004 European Peptide Society and John Wiley Sons. Ltd.
引用
收藏
页码：531 / 534
页数：4
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